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Chinese Journal of Chemistry 2024年第10期42卷 1107-1113页

作者： Guangyu Wang Huaiyuan Li Xuebing Leng Long Lu qilong shen Key Laboratory of Fluorine and Nitrogen Chemistry and Advanced Materials Shanghai Institute of Organic ChemistryUniversity of Chinese Academy of SciencesChinese Academy of Sciences345 Lingling LuShanghai 200032China

The invention of a well-defined Cu(Ⅲ)fluoride complex Me_(4)N^(+)[Cu(CF_(3))_(3)(F)]^(-)1 enabled to access a versatile of functionalized Cu(Ⅲ)complexes[Me_(4)N]^(+)[Cu(X)(CF_(3))_(3)]^(-)(X=C_(6)F_(5),C_(6)F_(5)C≡C,CN,Cl,N_(3),^(t)BuOO,SCN,OAc,SAr),many of them for the first time.The availability of these complexes allowed us to evaluate the trans-influence order of ligand in Cu(Ⅲ)complexes:Bn>CF_(3)^(-)>C_(6)F_(5)^(-)>N_(3)^(-)>py~CH_(3)^(-)~C_(6)F_(5)C≡C>NO_(2)PhO^(-)~^(t)BuOO^(-)~CH_(3)COO^(-)>F^(-).

关键词： Fluorine Copper Cu(Ⅲ) Cu(Ⅲ)fluoride Trifluoromethyl

A Versatile,Electrophilic Reagent for Monofluoromethylthiolation

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Chinese Journal of Chemistry 2023年第18期41卷 2317-2329页

作者： Rui Wang Long Lu qilong shen Key Laboratory of Organofluorine Chemistry Shanghai Institute of Organic ChemistryUniversity of Chinese Academy of SciencesChineseAcademyof Sciences345 Lingling RoadShanghai 200032China

Comprehensive Summary,A new electrophilic monofluoromethylthiolating reagent N-fluoromethylthiophthalimide PhthSCH2F 1 was developed.Reagent 1 could be readily synthesized from easily available starting materials benzyl mercaptan and CH_(2)FCl in three steps.N-Fluoromethylthiophthalimide 1 is a powerful electrophilic monofluoromethylthiolating reagent that allows the monofluoromethylthiolation of a wide range of nucleophiles including alkynes,aryl/vinyl boronic acids,electron-rich heteroarenes,β-ketoesters and oxindoles,as well as thiols under mild conditions.

关键词： Fluorine Monofluoromethylthiolation Electrophilic Sulfur

Stereoselective formation of Z-monofluoroalkenes by nickel-catalyzed defluorinative coupling of gem‑difluoroalkenes with lithium organoborates

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Chinese Chemical Letters 2022年第9期33卷 4277-4280页

作者： Yisa Xiao Weichen Huang qilong shen Key Laboratory of Organofluorine Chemistry Shanghai Institute of Organic ChemistryUniversity of Chinese Academy of SciencesChinese Academy of SciencesShanghai 200032China

A method for stereoselective construction of Z-monofluoroalkenes by nickel-catalyzed defluorinative coupling of gem‑difluoroalkenes in mild conditions was described.The combination of lithium organoborate and ZnBr_(2) generated in situ lithium aryl zincates,which facilitates the transmetalation step of the nickel-catalyzed cross coupling reaction.

关键词： gem‑Difluoroalkenes Lithium organoborate Defluorination Nickel Coupling

Neutral Five-Coordinate Arylated Copper(Ⅲ) Complex: Key Intermediate in Copper-Mediated Arene Trifluoromethylation

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Chinese Journal of Chemistry 2022年第16期40卷 1924-1930页

作者： Guangyu Wang Man Li Xuebing Leng Xiaosong Xue qilong shen Key Laboratory of Organofluorine Chemistry Shanghai Institute of Organic ChemistryUniversity of Chinese Academy of SciencesChinese Academy of Sciences345 Lingling LuShanghai200032 China Key Laboratory of Material Chemistry for Energy Conversion and Storage Ministry of EducationHubei Key Laboratory of Bioinorganic Chemistry and Materia MedicaHubei Key Laboratory of Materials Chemistry and Service FailureSchool of Chemistry and Chemical EngineeringHuazhong Universityof Scienceand TechnologyWuhanHubei 430074China

Five-coordinate neutral Cu(Ⅲ)complexes have long been considered as the key intermediates in copper-mediated/catalyzed arene trifluoromethylative reactions,but the identity of these complexes remains elusive.Herein,we reported,for the first time,the preparation and characterization of these putative complexes[(bpy)Cu(CF_(3))_(2)(C_(6)F_(4)R)]and investigation of their C(sp^(2))-CF_(3) bond-forming reductive elimination.Our mechanistic studies including kinetic studies,the effect of temperature and solvents,the effect of the para-substitution of the ligand as well as DFT calculations suggest that C(sp^(2))-CF_(3) reductive elimination process proceeds via synchronous bond-breaking/bond-forming process.

关键词： Cu(Ⅲ) Reductive elimination Trifluoromethyl Mechanism Concerted pathway

Nucleophilic Trifluoromethylthiolation of Alkyl Chlorides, Bromides and Tosylates

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Chinese Journal of Chemistry 2016年第5期34卷 495-504页

作者： Chunfa Xu Qingyun Chen qilong shen Key Laboratory of Organofluorine Chemistry Shanghai Institute of Organic Chem~try Shanghai 200032 China

有 AgSCF 3 的烷基氯化物，溴化物和 tosylates 的直接亲核的 trifluoromethylthiolation 被描述。这被发现 nBu 4 NI 或 nBu 4 NI/nBu 4 NBr 显著地提高了反应率。反应条件是温和的，因此允许许多功能的组的忍耐。

关键词： trifluoromethylthiolation 亲核氟的符号烷基卤化物

Chincona Alkaloid-Catalyzed Enantioselective Trifluoromethylthiolation of Oxindoles

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Chinese Journal of Chemistry 2014年第8期32卷 678-680页

作者： Tao Yang qilong shen Long Lu Key Laboratory of Organofluorine Chemistry Shanghai Institute of Organic ChemistryChinese Academy of SciencesShanghai 200032China

An organocatalytic asymmetric trifluoromethylthiolation of 3-aryl or 3-alkyloxindoles employing a trifluoromethyl-substituted thioperoxide as the electrophilic trifluoromethylthiolating reagent was described.Reactions occurred in good to excellent enantioselectivities to generate oxindoles with a SCF_(3)-substituted quaternary chiral center.

关键词： organocatalytic fluorine trifluoromethylthio asymmetric oxindole

Monofluoromethyl-Substituted Sulfonium Ylides:Preparation,Structure-Reactivity Study and Substrate Scope

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Chinese Journal of Chemistry 2020年第11期38卷 1317-1331页

作者： Xin Hong Yafei Liu Long Lu qilong shen Key Laboratory of Orgonofluorine Chemistry Center for Excellence in Molecular SynthesisShanghai Institute of Organic ChemistryUniversity of Chinese Academy of SciencesChinese Academy of Sciences345 Lingling RoadShanghai 200032China Shanghai Institute of Organic Chemistry University of Chinese Academy of SciencesChinese Academy of Sciences345 Ling ling RoadShanghai 200032China

of main observation and conclusion Structure-reactivity study of a family of electrophilic monofluoromethylating reagents based on sulfonium ylide skeleton with different steric hindrance and electron-withdrawing properties was described.These studies led us to discover two highly reactive reagents 3 with a cyclic malonate backbone and 6 with an electron-poor 1,1,1,5,5,5-hexafluoropentane-2,4-dione backbone.The high reactivity of reagent 6 allowed to highly selectively access either C-monofluoromethylated or O-monofluoromethylated p-ketoesters in high yields by the use of different bases.In addition,reactions of reagent 3 with a variety of nucleophiles including phenols,carboxylic acids,thiophenols or heteroaryl nucleophiles occurred in full conversion within 10 min at room temperature and the scopes for these reactions were reported in detail.

关键词： backbone reagent reactivity

A Fruitful Decade of Organofluorine Chemistry: New Reagents and Reactions

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CCS Chemistry 2022年第8期4卷 2518-2549页

作者： Feng-Ling Qing Xin-Yuan Liu Jun-An Ma qilong shen Qiuling Song Pingping Tang Key Laboratory of Organofluorine Chemistry Shanghai Institute of Organic ChemistryChinese Academy of SciencesShanghai 200032 shenzhen Grubbs Institute Department of ChemistryGuangdong Provincial Key Laboratory of CatalysisSouthern University of Science and TechnologyShenzhen 518055 Department of Chemistry Tianjin UniversityTianjin 300072 Institute of Next Generation Matter Transformation College of Chemical EngineeringHuaqiao UniversityFujian 361021 State Key Laboratory Institute of Elemento-Organic ChemistryCollege of ChemistryNankai UniversityTianjin 300071

The development of synthetic methods for the introduction of the fluorine atom and fluoroalklyl groups into organic molecules has gained increased attention.Synthetic organic chemists have recently jumped into the field of organofluorine chemistry and have thus made significant contributions.Furthermore,these newly developed methods are typically safer and more effective than the traditional methods.In this review,wewill summarize the representative contributions of new reagents and reactions developed in the past decade.

关键词： fluorination fluoroalkylation reagent reaction fluorine chemistry

Asymmetric Difluoromethylthiolation of Carbon Nucleophiles with Optically Pure Difluoromethylthiolating Reagents Derived from Camphorsultam

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Chinese Journal of Chemistry 2019年第10期37卷 1041-1050页

作者： He Zhang Xiaolong Wan qilong shen Key Laboratory of Organofluorine Chemistry Center for Excellence in Molecular SynthesisShanghai Institute of Organic ChemistryUniversity of Chinese Academy of SciencesChinese Academy of Sciences345 Lingling LuShanghai 200032China

The invention of a family of optically pure electrophilic difluoromethylthiolating reagents 9a-c based on the camphorsultam skeleton was described.These reagents reacted with a variety of soft carbon nucleophiles such... 详细信息

关键词： thiol skeleton Reagent

Pentafluoroethylbenziodoxole （BIX-C2Fs）： A Shelf-Stable Reagent for Pentafluoroethylation of β-Ketoesters and Arylboronic Acids

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Chinese Journal of Chemistry 2016年第7期34卷 662-668页

作者： Jiansheng Zhu Yuguang Li Chuanfa Ni qilong shen Key Laboratory of Organofluorine Chemistry Shanghai Institute of Organie Chemistry Chinese Academy of Sciences Shanghai 200032 China

An improved method for the preparation of pentafluoroethylating reagent pentafluoroethyl-substituted benzio- doxole （BIX-C2Fs） was described. Under mild conditions, BIX-C2F5 was able to react with β-ketoesters or a... 详细信息

关键词： fluorine pentafluoroethyl hypervalent electrophilic cross-coupling